Picolinic acid → HCID 11589598, compound

HRID 636267Notes

Reaction equation

HRID 636267 reaction equation
[Si:1]([O:18][C@@H:19]1[C@H:24]([CH3:25])[C@H:23](O)[CH2:22][C@H:21]([C:27]([O:29][CH3:30])=[O:28])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1C(O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CCOC(C)=O.O>[C:27]([C@@H:21]1[CH2:20][C@H:19]([O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:24]([CH3:25])=[CH:23][CH2:22]1)([O:29][CH3:30])=[O:28]

Participants

8

Reactant 4

HCID 1018Picolinic acidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11697580HCID 11697580, compound

Product 1

HCID 11589598HCID 11589598, compoundYield 88.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.2.c (R=Me, P=TBDPS, A=COOCH3) (167 mg, 0.392 mmol), picolinic acid (257 mg, 2.092 mmol) and triphenylphosphine (548 mg, 2.092 mmol) in THF at −38° C. was added dropwise DIAD (diisopropyl azodicarboxylate; 412 μL, 2.092 mmol) over 4 min. The reaction solution was stirred for 4.5 h and warmed to room temperature overnight. The mixture was poured into water and EtOAc (50 ml:50 ml). The organic phase was separated, the aqueous layer was extracted with EtOAc (3×50 ml) and dried over MgSO4. The residue was separated by HPLC (isooctane/EtOAc 98:2), affording (4S,6S)-4-carbomethoxy-6-t-butyldiphenylsilyloxy-1-methylcyclohexene (142 mg, 88.8%) as a colorless oil.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted with EtOAc (3×50 ml)
  3. dry with materialdried over MgSO4
  4. customThe residue was separated by HPLC (isooctane/EtOAc 98:2)

Sources & evidence

ORD record
ord-d85155cf8e8a4c3d8847e4cd6de2842c
Source dataset
uspto-grants-2001_02
Patent number
US06191292B1

Reaction notes

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